Eclalbasaponin I

Details

• Internal ID: 6881ba4d-5e5e-4c37-97f8-ddae35355e7f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C42H68O14/c1-37(2)14-15-42(36(52)56-35-33(51)31(49)29(47)23(19-44)54-35)21(16-37)20-8-9-25-39(5)12-11-27(55-34-32(50)30(48)28(46)22(18-43)53-34)38(3,4)24(39)10-13-40(25,6)41(20,7)17-26(42)45/h8,21-35,43-51H,9-19H2,1-7H3/t21-,22+,23+,24-,25+,26+,27-,28+,29+,30-,31-,32+,33+,34-,35-,39-,40+,41+,42+/m0/s1
• InChI Key: ZKMRZIYTCZLEAV-VVJIWJAZSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₄
• Molecular Weight: 797.00 g/mol
• Exact Mass: 796.46090684 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• 158511-59-2
• [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• DTXSID501316627
• ((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• RefChem:136257
• DTXCID201746465
• CHEMBL3343908
• ecliptasaponin C
• Eclalbasaponin I (Standard)
• orb1297387
• orb3140385
• SCHEMBL30637474
• HY-N7022R
• HY-N7022
• IGA51159
• BDBM50235144
• AKOS040760374
• EBC-617700
• (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
• DA-63109
• MS-31467
• CS-0101588
• E88622
• 1-O-[3beta-(beta-D-Glucopyranosyloxy)-16alpha-hydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3666	36.66%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.5092	50.92%
P-glycoprotein inhibitior	+	0.7507	75.07%
P-glycoprotein substrate	-	0.8390	83.90%
CYP3A4 substrate	+	0.7114	71.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.5866	58.66%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.8224	82.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.6955	69.55%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9348	93.48%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8519	85.19%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7102	71.02%
Androgen receptor binding	+	0.7186	71.86%
Thyroid receptor binding	-	0.5868	58.68%
Glucocorticoid receptor binding	+	0.6176	61.76%
Aromatase binding	+	0.6083	60.83%
PPAR gamma	+	0.7174	71.74%
Honey bee toxicity	-	0.7477	74.77%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6005	60.05%
Fish aquatic toxicity	+	0.9411	94.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	9.581 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.43%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.41%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.20%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.07%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.43%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	84.91%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.50%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.46%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.30%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.88%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.33%	97.25%
CHEMBL2581	P07339	Cathepsin D	80.37%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.16%	89.00%

Plants that contains it

• Eclipta prostrata

Cross-Links

• PubChem: 10079039
• LOTUS: LTS0163297
• wikiData: Q104400183